Methionine Sulfoxide Reductase as an Efficient Catalyst for Kinetic Resolution of the Chiral Sulfoxides DOI
Benjamin List, Jan Samsonowicz‐Górski

Synfacts, Journal Year: 2023, Volume and Issue: 19(07), P. 0712 - 0712

Published: June 16, 2023

Key words chiral sulfoxides - kinetic resolution reductases rational mutagenesis

Language: Английский

Expanding the toolbox of Baeyer–Villiger and flavin monooxygenase biocatalysts for the enantiodivergent green synthesis of sulfoxides DOI Creative Commons
Jingyue Wu, Silvia Anselmi, Alexandra T. P. Carvalho

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(15), P. 8685 - 8693

Published: Jan. 1, 2024

Two new monooxygenase biocatalysts, the Baeyer-Villiger BVMO145 and flavin FMO401 from Almac library, have been found to catalyse enantiodivergent oxidation of sulfides bearing N-heterocyclic substituents into sulfoxides under mild green conditions. The biocatalyst provides (

Language: Английский

Citations

6
A Green Environmental Protection Photocatalytic Molecular Reactor for Aerobic Oxidation of Sulfide to Sulfoxide DOI
Jiaqi Chen,

Kai‐Yang Zhang,

Xiudu Zhang

et al.

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 30(12)

Published: Nov. 30, 2023

Abstract The design and synthesis of metal‐organic frameworks (MOFs) as photocatalytic molecular reactors for varied reactions have drawn great attention. In this work, we designed a novel photoactive perylenediimides‐based (PDI) carboxylate ligand N,N’‐di(3’,3”,5’,5”‐tetrakis(4‐carboxyphenyl))‐1,2,6,7‐tetrachloroperylene‐3,4,9,10‐tetracarboxylic acid diimide (Cl‐PDI‐TA) use it to successfully synthesize Zr(IV)‐based MOF 1 constructed from [Zr 6 O 8 (H 2 O) ] 8+ clusters bridged by Cl‐PDI‐TA ligands. Structural analysis revealed that Zr‐MOF manifests 3D framework with (4,8)‐connected csq topology possesses triangular channels ~17 Å mesoporous hexagonal ~26 along c ‐axis. Moreover, the synthesized exhibits visible‐light absorption efficient photoinduced free radical generation property, making promising reactor. When was used photocatalyst aerobic oxidation sulfides under irradiation visible light, could afford corresponding sulfoxides high yield selectivity. Experimental results demonstrated substrate be fixed in pores directly transformed products solid state. Furthermore, mechanism transformation also investigated singlet oxygen ( ) superoxide (O ⋅ − generated energy transfer electron photoexcited oxidants were main active species catalytic reactions. This work offers perceptive comprehension PDI‐based MOFs further study on

Language: Английский

Citations

11
Cooperative chemoenzymatic and biocatalytic cascades to access chiral sulfur compounds bearing C(sp3)–S stereocentres DOI Creative Commons
Fei Zhao,

Ariane Mattana,

R. Alam

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: Sept. 27, 2024

Language: Английский

Citations

3
Engineering of Methionine Sulfoxide Reductase A with Expanded Substrate Scope for Deracemization of Sulfinyl Esters DOI

Xu Jiang,

Yanli Chen,

Shihuan Zhou

et al.

ACS Sustainable Chemistry & Engineering, Journal Year: 2024, Volume and Issue: 12(32), P. 11987 - 11996

Published: July 29, 2024

Chiral sulfinyl esters are an essential source for preparation of chiral sulfur-containing fine chemicals and pharmaceuticals. However, sustainable enantioselective syntheses optically pure remain to be explored. Herein, we have developed methionine sulfoxide reductase A (MsrA) variants with expanded substrate scope using in silico docking semirational mutagenesis techniques, aimed at preparing enantiopure esters. The variant paMsrA-F59A exhibited exceptional activity enantioselectivity across various esters, yielding the R enantiomers approximately 50% yield 99% enantiomeric excess. Furthermore, this overcame significant limitation wild-type (WT) MsrA, broadening its from methyl ethyl substituents n-propyl/butyl ester substituents. Afterward, by employing conjunction oxidase styrene monooxygenase (SMO), achieved cyclic deracemization racemic obtaining a series (R)-sulfinyl >90% This study successfully providing environmentally friendly strategy efficiently Moreover, our extended application MsrA synthesis compounds bulkier frameworks, highlighting potential green chemistry applications.

Language: Английский

Citations

2
Perylene diimide-based hyper-cross-linked polymers for visible-light-driven selective organic sulfide oxidation DOI

Zi-Yi Zhao,

Sijia Wang,

Long-Bo Mi

et al.

Separation and Purification Technology, Journal Year: 2024, Volume and Issue: 359, P. 130543 - 130543

Published: Nov. 14, 2024

Language: Английский

Citations

1
Cyclic Deracemization of rac‐Sulfoxides via Alternating Biocatalytic Reduction and Light‐Dependent Oxidation Employing Eosin Y as Photocatalyst DOI Creative Commons
Sarah Bierbaumer, Silvia M. Glueck, Christoph K. Winkler

et al.

ChemCatChem, Journal Year: 2024, Volume and Issue: 16(15)

Published: Feb. 21, 2024

Abstract The synergistic combination of biocatalysis and photocatalysis is emerging as powerful tool for the development sustainable atom‐efficient synthetic concepts facilitating an enormous portfolio possible reactions which even goes beyond capabilities found in nature. Here, a cyclic deracemization process presented tailored synthesis optically pure sulfoxides are versatile structural motifs asymmetric well bioactive compounds. Enantioselective enzyme‐catalyzed reduction rac ‐sulfoxides was combined with stereo‐unselective photocatalytic oxidation corresponding sulfide intermediate. utilization readily accessible rather inexpensive photocatalyst Eosin Y increases usability this method. To overcome incompatibility between biocatalytic step, performed step‐wise fashion via alternated darkness under illumination. This modular system allowed precise adjustments reaction parameters yielding desired sulfoxide targets up to >99 % ee . Evaluation substrate scope including range structurally diverse molecules demonstrated its broad applicability.

Language: Английский

Citations

0
Deracemization of Sulfoxides Combining Electrocatalysis and Biocatalysis DOI

Xinyu Duan,

Dong Cui,

Mengdi Wang

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(23), P. 3107 - 3112

Published: Aug. 13, 2024

Comprehensive Summary The concurrent implementation of cascade reactions that combine biocatalysis and chemocatalysis is a challenging undertaking. Electrocatalysis provides versatile catalytic abilities allows for mild reaction conditions, offering the potential designing chemoenzymatic reactions. research on bioelectrocatalysis has primarily concentrated utilizing electrocatalysis to achieve cofactor regeneration enzymes. In contrast with previous reports, herein, we developed deracemization strategy involving combination biocatalytic reduction anodic oxidation in an undivided cell chiral sulfoxides, demonstrating good compatibility. We anticipate this study will offer alternative pathway design combined biocatalysis.

Language: Английский

Citations

0
Characterization and mechanism investigation of salt-activated methionine sulfoxide reductase A from halophile DOI Creative Commons

Shihuan Zhou,

Bochen Pan,

Xiaoxue Kuang

et al.

iScience, Journal Year: 2024, Volume and Issue: 27(9), P. 110806 - 110806

Published: Aug. 23, 2024

Halophiles, thriving in harsh saline environments, capture scientific interest due to their remarkable ability prosper under extreme salinity. This study unveils the distinct salt-induced activation of methionine sulfoxide reductases (MsrA) from

Language: Английский

Citations

0
Discovery and biocatalytic exploration of fungal ene-reductases DOI Creative Commons
Pedro Henrique Damada

Published: Aug. 20, 2024

Old Yellow Enzymes (OYEs) catalyze the double bond reduction of α,β–unsaturated compounds, particularly those possessing an electron-withdrawing group. This is interest to synthetic chemistry applications that target synthesis enantiomerically pure compounds. OYEs surpass chemical catalysts due their high enantioselectivity/stereoselectivity and operability under mild conditions. The first OYE was described in 1932, hence its name. Many other OYE-type reductases have since been discovered, yet numerous ene-reductases remain undiscovered across diverse sources. Recent classification categorizes these enzymes into seven classes based on sequence structural features. study concentrated from fungi, specifically Penicillium citrinum CBMAI 1186 steckii (both mesophilic species), along with Aspergillus thermomutatus, Chaetomium thermophilium, Lachancea thermotolerans, Ogatae polymorpha Thermothielavioides terrestris (all mesothermophilic species). involving P. involved whole-cell reactions reduce α,β,γ,δ–unsaturated For steckii, eleven OYE-encoding genes were selected, yielding six expressed purified enzymes. Characterization included reaction rates, thermostability, pH optimum, substrate acceptance. To broaden toolbox robust variants, five thermophilic fungi selected for exploratory biocatalytic resulted production characterization thermostable OYEs. Next, four newly discovered performing conversions using Escherichia coli. When a biphasic system, efficient could be achieved. In summary, this work focused acquisition, examination, application fungal OYEs, contribute new insights complement existing understanding enzyme group, while enriching available biocatalysis, thereby expanding prospects future applications.

Language: Английский

Citations

0
Hot off the Press DOI
Robert A. Hill, Andrew Sutherland

Natural Product Reports, Journal Year: 2023, Volume and Issue: 40(6), P. 1066 - 1070

Published: Jan. 1, 2023

A personal selection of 32 recent papers is presented covering various aspects current developments in bioorganic chemistry and novel natural products such as jasminoxepinone from Jasminum sambac .

Language: Английский

Citations

0